A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

Aimin Song; Xiaobing Wang; Kit Lam

doi:10.1016/S0040-4039(03)00108-4

A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

Aimin Song, Xiaobing Wang, Kit Lam

Biochemistry and Molecular Medicine

Research output: Contribution to journal › Article

146 Scopus citations

Abstract

Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

Original language	English (US)
Pages (from-to)	1755-1758
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(03)00108-4
State	Published - Feb 24 2003

Keywords

Coumarin-3-carboxylic acids
Knoevenagel condensation
Meldrum's acid

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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Song, A., Wang, X., & Lam, K. (2003). A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones. Tetrahedron Letters, 44(9), 1755-1758. https://doi.org/10.1016/S0040-4039(03)00108-4

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AU - Lam, Kit

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AB - Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

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